On November 24, 1819, Riley wrote a letter from Fort Wayne to B. Sanford, Esq., advising him that he had concluded his surveys for the season but wanted:

“... to examine for myself the practicality of so uniting the Wabash with the Maumee as to render intercourse by water between the Ohio river and Lake Erie safe and easy through this channel.... The little Wabash rises in an elevated swamp prairie six miles south of Fort Wayne, and joins the Wabash eighteen miles hence. Thus in high stages of water, a portage of only six miles carries merchandise from the level of the Maumee into the navigable waters of the Wabash (and vice versa).”[5]

These observations by Riley on the possibility of a canal were supplemented in the same letter by his early impression of Fort Wayne as a future center of population. He stated to Mr. Sanford:

The country around Fort Wayne is very fertile. The situation is commanding and healthful.... Here will arise a town of great importance, which must become a depot of immense trade. The fort is now only a small stockade; no troops are stationed here, and less than thirty dwelling houses occupied by French and American families form the whole settlement.[6]

Riley added that the departure of the soldiers had left this little band of residents extremely lonely, but he predicted that as soon as the lands were opened for sale the settlers would flock to this region. The people living at Fort Wayne at this time had no right to the land and were considered as “squatters” by the government officials.

Possibly the most interesting letter that James Riley wrote from Fort Wayne was written near the close of the surveying season in 1820. It was addressed to Edward Tiffin, Surveyor General. Riley had been in the neighborhood of Fort Wayne, when a snow storm forced him to discontinue his work temporarily. Taking advantage of his free time, Riley came to Fort Wayne to witness the annual distribution of the annuities to the Indians gathered there. After speaking highly of the natural advantages of the site of Fort Wayne, Riley urged that the government land be offered for sale as soon as possible, saying:

There are now in its [Fort Wayne] immediate vicinity, more than 40 families of ‘Squatters’ and traders, besides a great number of young men each with his bundle or shop, of goods and trinkets; all of whom are depredating on the public lands, for timber for their numberous buildings, for fire-wood, &c. &c.; and as they have not interest in the soil, and little hope of being able to purchase the land when sold, a system of waste and destruction is going on, and is apparently entered into by all.[6a]

Riley then added another reason why the lands should be sold. He wrote:

There are now assembled, as I should judge, at least one thousand persons from Ohio, Michigan, Indiana, and New York, whose object is stated to be that of trade with the Indians, in order to carry off some of their specie, paid them by the Government. They have brought whiskey in abundance, which they pretend to deposit with agent, until he shall have finished his business with the Indians, but yet contrive to deal out large quantities from their deposits in the woods, so that the savages are kept continually drunk, and unfit for any business. Horse-racing, drinking, gambling, and every kind of debauchery, extravagance and waste, are the order of the day, and night too; and in my opinion, the savages themselves are the most christianized, and least savage, of the two classes now congregated here. Here the whites set example to the Indians too indelicate to mention, and that cannot fail to produce in their minds disgust for the American character.[7]

Riley concluded by saying: